Graduated from New York University in 1900 with a degree in English literature, and returned to earn a master's degree in English in 1904. He went on to Harvard University for a second Master's and received his Ph.D. in 1907. He taught at Harvard University, Yale University, and Smith College before coming to Vassar in 1915. MacCracken was Vassar's fifth president and his tenure was the longest in the college's history. He sparked controversy because of his advocacy for women's suffrage and his liberal views toward education and politics. He was fired in 1918 because of these views but returned to office after student-faculty protests and the resignation of three trustees. MacCracken contributed many important things to Vassar including service as an English professor and the endowment of a chair in the English department. He also worked to bring more foreign students to Vassar, increased student involvement in college policy making, established the Euthenics Department (1923), and supported Hallie Flanagan Davis in her work on the Experimental Theatre. MacCracken worked tirelessly through both world wars, spearheading Vassar's many contributions to the war effort. He also worked with the Red Cross and served as director of educational work on the New York Council of Home Defense. He was a member of the National Committee of the League to Enforce Peace, an organizer for the Dutchess County Health Association, (the first county public health organization in the United States), and one of the creators of the Kosciuszko Foundation to promote relations between the United States and Poland. He was a key figure in the foundation of Sarah Lawrence College in 1926, a member of the National Conference of Christians and Jews, and chairman of the conference's international meeting in London. MacCracken died May 7, 1970 in Poughkeepsie at the age of 89.